ES2908773T3 - Derivados de 5-(2-(2,5-difluorofenil)pirrolidin-1-il)-3-(1H-pirazol-1-il)pirazolo[1,5-a]pirimidina y compuestos relacionados como inhibidores de Trk quinasa para el tratamiento del cáncer - Google Patents

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Publication number

ES2908773T3

ES2908773T3 ES18836977T ES18836977T ES2908773T3 ES 2908773 T3 ES2908773 T3 ES 2908773T3 ES 18836977 T ES18836977 T ES 18836977T ES 18836977 T ES18836977 T ES 18836977T ES 2908773 T3 ES2908773 T3 ES 2908773T3

Authority

ES

Spain

Prior art keywords

pyrazolo

pyrrolidin

pyrazol

difluorophenyl

pyrimidine

Prior art date

2017-12-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 221
• 206010028980 Neoplasm Diseases 0.000 title claims description 66
• 201000011510 cancer Diseases 0.000 title claims description 36
• 238000011282 treatment Methods 0.000 title description 26
• FWDOVLGKHCXRFF-UHFFFAOYSA-N FC1=C(C=C(C=C1)F)C1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC=C1 Chemical class FC1=C(C=C(C=C1)F)C1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC=C1 FWDOVLGKHCXRFF-UHFFFAOYSA-N 0.000 title description 2
• 229940043355 kinase inhibitor Drugs 0.000 title description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 92
• 150000003839 salts Chemical class 0.000 claims abstract description 79
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 78
• 239000012453 solvate Substances 0.000 claims abstract description 56
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 49
• 150000002367 halogens Chemical class 0.000 claims abstract description 48
• 125000003118 aryl group Chemical group 0.000 claims abstract description 28
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 28
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 22
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
• 125000004429 atom Chemical group 0.000 claims abstract description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 13
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
• 229910003827 NRaRb Inorganic materials 0.000 claims abstract description 9
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 9
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims abstract description 7
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 6
• 229910052701 rubidium Inorganic materials 0.000 claims abstract description 6
• 229910052702 rhenium Inorganic materials 0.000 claims abstract description 3
• 229910052703 rhodium Inorganic materials 0.000 claims abstract description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 148
• 208000035475 disorder Diseases 0.000 claims description 78
• 201000010099 disease Diseases 0.000 claims description 70
• 229910052731 fluorine Inorganic materials 0.000 claims description 70
• -1 (Ca-Cio) Chemical group 0.000 claims description 62
• 230000004927 fusion Effects 0.000 claims description 48
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 44
• 230000002401 inhibitory effect Effects 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 13
• 230000001404 mediated effect Effects 0.000 claims description 12
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• ZXYOEGYYCHOXLT-CQSZACIVSA-N 5-[(2R)-2-(3,6-difluoropyridin-2-yl)pyrrolidin-1-yl]-3-(4-methylpyrazol-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound CC1=CN(N=C1)C1=C2N=C(C=CN2N=C1)N1CCC[C@@H]1C1=NC(F)=CC=C1F ZXYOEGYYCHOXLT-CQSZACIVSA-N 0.000 claims description 6
• OXLGFSVYEYBBDZ-LJQANCHMSA-N 1-[1-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]-N,N-dimethylmethanamine Chemical compound C=1(C=NN(C=1)C1=C2N=C(N3[C@H](CCC3)C3=C(C=CC(F)=C3)F)C=CN2N=C1)CN(C)C OXLGFSVYEYBBDZ-LJQANCHMSA-N 0.000 claims description 5
• HHRDXXMUPDELIS-UHUGOGIASA-N 1-[1-[5-[(2R)-2-(3-fluoropyridin-2-yl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]pyrrolidin-3-ol Chemical compound FC=1C(=NC=CC=1)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)N1CC(CC1)O HHRDXXMUPDELIS-UHUGOGIASA-N 0.000 claims description 5
• BJWFEKVBDBMJOM-GOSISDBHSA-N 3-[1-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CN(N=C1)C1=C2N=C(C=CN2N=C1)N1CCC[C@@H]1C1=C(F)C=CC(F)=C1 BJWFEKVBDBMJOM-GOSISDBHSA-N 0.000 claims description 5
• FSERQXAZXYLBNL-GOSISDBHSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-[4-(methoxymethyl)pyrazol-1-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)COC FSERQXAZXYLBNL-GOSISDBHSA-N 0.000 claims description 5
• WQJAFTXYVSMMQO-OAQYLSRUSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-[4-(oxan-4-yl)pyrazol-1-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C1CCOCC1 WQJAFTXYVSMMQO-OAQYLSRUSA-N 0.000 claims description 5
• FWDOVLGKHCXRFF-MRXNPFEDSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-pyrazol-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound FC1=CC([C@H]2CCCN2C2=NC3=C(C=NN3C=C2)N2C=CC=N2)=C(F)C=C1 FWDOVLGKHCXRFF-MRXNPFEDSA-N 0.000 claims description 5
• IFEYPPSMVUHFEX-LJQANCHMSA-N 5-[(2R)-2-(3,6-difluoropyridin-2-yl)pyrrolidin-1-yl]-3-[4-(5-methoxypyridin-3-yl)pyrazol-1-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC=1C(=NC(=CC=1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C=1C=NC=C(C=1)OC IFEYPPSMVUHFEX-LJQANCHMSA-N 0.000 claims description 5
• NKOLSNLRDIPVJR-OAHLLOKOSA-N 5-[(2R)-2-(3-fluoro-6-methoxypyridin-2-yl)pyrrolidin-1-yl]-3-(4-methylpyrazol-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound COC1=CC=C(F)C(=N1)[C@H]1CCCN1C1=NC2=C(C=NN2C=C1)N1C=C(C)C=N1 NKOLSNLRDIPVJR-OAHLLOKOSA-N 0.000 claims description 5
• JODKEDGKZUWACK-MRXNPFEDSA-N 5-fluoro-N,N-dimethyl-6-[(2R)-1-[3-(4-methylpyrazol-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl]pyridin-2-amine Chemical compound CN(C)C1=NC([C@H]2CCCN2C2=NC3=C(C=NN3C=C2)N2C=C(C)C=N2)=C(F)C=C1 JODKEDGKZUWACK-MRXNPFEDSA-N 0.000 claims description 5
• SLWZFZMCROXTBB-HXUWFJFHSA-N CC1=C(C(C)=NO1)C1=CN(N=C1)C1=C2N=C(C=CN2N=C1)N1CCC[C@@H]1C1=C(F)C=CC(F)=C1 Chemical compound CC1=C(C(C)=NO1)C1=CN(N=C1)C1=C2N=C(C=CN2N=C1)N1CCC[C@@H]1C1=C(F)C=CC(F)=C1 SLWZFZMCROXTBB-HXUWFJFHSA-N 0.000 claims description 5
• RZDNAELBSZNRMA-GOSISDBHSA-N COC1=CC=C(C=N1)C1=CN(N=C1)C1=C2N=C(C=CN2N=C1)N1CCC[C@@H]1C1=NC(F)=CC=C1F Chemical compound COC1=CC=C(C=N1)C1=CN(N=C1)C1=C2N=C(C=CN2N=C1)N1CCC[C@@H]1C1=NC(F)=CC=C1F RZDNAELBSZNRMA-GOSISDBHSA-N 0.000 claims description 5
• OQZKOMRUKNROFF-HXUWFJFHSA-N FC1=CC([C@H]2CCCN2C2=NC3=C(C=NN3C=C2)N2C=C(C=N2)C(=O)N2CCOCC2)=C(F)C=C1 Chemical compound FC1=CC([C@H]2CCCN2C2=NC3=C(C=NN3C=C2)N2C=C(C=N2)C(=O)N2CCOCC2)=C(F)C=C1 OQZKOMRUKNROFF-HXUWFJFHSA-N 0.000 claims description 5
• QPSBIRQTQQJSAV-XMMPIXPASA-N FC1=CC([C@H]2CCCN2C2=NC3=C(C=NN3C=C2)N2C=C(C=N2)C2=CC(OC3COC3)=CN=C2)=C(F)C=C1 Chemical compound FC1=CC([C@H]2CCCN2C2=NC3=C(C=NN3C=C2)N2C=C(C=N2)C2=CC(OC3COC3)=CN=C2)=C(F)C=C1 QPSBIRQTQQJSAV-XMMPIXPASA-N 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• YAQRMLFNKOAITD-GOSISDBHSA-N 1-[1-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]ethanone Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C(C)=O YAQRMLFNKOAITD-GOSISDBHSA-N 0.000 claims description 4
• ADEQOCVYRHUSQD-HSZRJFAPSA-N FC1=CC([C@H]2CCCN2C2=NC3=C(C=NN3C=C2)N2C=C(C=N2)C2=CC=C(OC3COC3)N=C2)=C(F)C=C1 Chemical compound FC1=CC([C@H]2CCCN2C2=NC3=C(C=NN3C=C2)N2C=C(C=N2)C2=CC=C(OC3COC3)N=C2)=C(F)C=C1 ADEQOCVYRHUSQD-HSZRJFAPSA-N 0.000 claims description 4
• ZUSMIJRMTPRXTJ-OAHLLOKOSA-N N-methyl-3-(4-methylpyrazol-1-yl)-N-[(1R)-1-phenylethyl]pyrazolo[1,5-a]pyrimidin-5-amine Chemical compound C1(=CN(N=C1)C1=C2N(N=C1)C=CC(N(C)[C@@H](C1=CC=CC=C1)C)=N2)C ZUSMIJRMTPRXTJ-OAHLLOKOSA-N 0.000 claims description 4
• JYIMXKQKLPLRNQ-QGZVFWFLSA-N [1-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]methanol Chemical compound C=1(C=NN(C=1)C1=C2N=C(N3[C@H](CCC3)C3=C(F)C=CC(F)=C3)C=CN2N=C1)CO JYIMXKQKLPLRNQ-QGZVFWFLSA-N 0.000 claims description 4
• NRNPLYYLKPVNIC-GOSISDBHSA-N 2-[1-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]-5-methyl-1,3,4-oxadiazole Chemical compound CC1=NN=C(O1)C1=CN(N=C1)C1=C2N=C(C=CN2N=C1)N1CCC[C@@H]1C1=C(F)C=CC(F)=C1 NRNPLYYLKPVNIC-GOSISDBHSA-N 0.000 claims description 3
• UAXGJOWHWARXQB-MRXNPFEDSA-N 3-[4-(difluoromethyl)pyrazol-1-yl]-5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC(C=1C=NN(C=1)C=1C=NN2C=1N=C(C=C2)N1[C@H](CCC1)C1=C(C=CC(=C1)F)F)F UAXGJOWHWARXQB-MRXNPFEDSA-N 0.000 claims description 3
• OCBCYGLEPKQJLG-JOCHJYFZSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-[4-(5-methoxypyridin-3-yl)pyrazol-1-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C=1C=NC=C(C=1)OC OCBCYGLEPKQJLG-JOCHJYFZSA-N 0.000 claims description 3
• OAKZLEZKMVHSHC-LJQANCHMSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-[4-(oxetan-3-yloxy)pyrazol-1-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)OC1COC1 OAKZLEZKMVHSHC-LJQANCHMSA-N 0.000 claims description 3
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
• QKVSHHHMLRSYER-OAHLLOKOSA-N C=1(C=NN(C=1)C1=C2N=C(N3[C@H](CCC3)C3=C(C=CC=N3)F)C=CN2N=C1)C Chemical compound C=1(C=NN(C=1)C1=C2N=C(N3[C@H](CCC3)C3=C(C=CC=N3)F)C=CN2N=C1)C QKVSHHHMLRSYER-OAHLLOKOSA-N 0.000 claims description 3
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 2
• BXMJUVFWPZJJBT-HXUWFJFHSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-(4-pyrimidin-5-ylpyrazol-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C=1C=NC=NC=1 BXMJUVFWPZJJBT-HXUWFJFHSA-N 0.000 claims 4
• GWBKXZDPLGYFKL-GOSISDBHSA-N FC=1C(=NC(=CC=1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C1=CC=NC=C1 Chemical compound FC=1C(=NC(=CC=1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C1=CC=NC=C1 GWBKXZDPLGYFKL-GOSISDBHSA-N 0.000 claims 4
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 2
• XPNRQOFDSVATHP-GOSISDBHSA-N 2-[1-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]ethanol Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)CCO XPNRQOFDSVATHP-GOSISDBHSA-N 0.000 claims 2
• YPELMYCNROOBTL-GOSISDBHSA-N 2-[1-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]propan-2-ol Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C(C)(C)O YPELMYCNROOBTL-GOSISDBHSA-N 0.000 claims 2
• HBLSATXZAMOVSK-HXUWFJFHSA-N 3-(4-diethylphosphorylpyrazol-1-yl)-5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)P(CC)(CC)=O HBLSATXZAMOVSK-HXUWFJFHSA-N 0.000 claims 2
• XMVDTTWJPOUEQE-CQSZACIVSA-N 3-(4-methylpyrazol-1-yl)-N-[(1R)-1-phenylethyl]pyrazolo[1,5-a]pyrimidin-5-amine Chemical compound C[C@@H](NC1=NC2=C(C=NN2C=C1)N1C=C(C)C=N1)C1=CC=CC=C1 XMVDTTWJPOUEQE-CQSZACIVSA-N 0.000 claims 2
• DTSSISWXVSDVEG-GOSISDBHSA-N 3-[1-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]-1,1-bis(methylsulfonyl)urea Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)NC(N(S(=O)(=O)C)S(=O)(=O)C)=O DTSSISWXVSDVEG-GOSISDBHSA-N 0.000 claims 2
• OFCFPJTYMSVMDW-OAQYLSRUSA-N 4-[1-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]-1-methylpyridin-2-one Chemical compound CN1C=CC(=CC1=O)C1=CN(N=C1)C1=C2N=C(C=CN2N=C1)N1CCC[C@@H]1C1=C(F)C=CC(F)=C1 OFCFPJTYMSVMDW-OAQYLSRUSA-N 0.000 claims 2
• SKMQZCZYTWTLGJ-OAQYLSRUSA-N 4-[1-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]pyrazol-4-yl]pyridine-3-carboxamide Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C1=CC=NC=C1C(=O)N SKMQZCZYTWTLGJ-OAQYLSRUSA-N 0.000 claims 2
• DOAYPAWWMMRURC-QGZVFWFLSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-(3-methoxy-5-methylpyrazol-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=C(C=C1C)OC DOAYPAWWMMRURC-QGZVFWFLSA-N 0.000 claims 2
• IQIWFTJAEREFNO-GOSISDBHSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-(4-dimethylphosphorylpyrazol-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)P(C)(C)=O IQIWFTJAEREFNO-GOSISDBHSA-N 0.000 claims 2
• ATDSJVXRQZIOOZ-OAQYLSRUSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-(4-pyridin-3-ylpyrazol-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C=1C=NC=CC=1 ATDSJVXRQZIOOZ-OAQYLSRUSA-N 0.000 claims 2
• OAUDLINPJVTIOT-HXUWFJFHSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-(4-thiophen-3-ylpyrazol-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C1=CSC=C1 OAUDLINPJVTIOT-HXUWFJFHSA-N 0.000 claims 2
• KHJVGVHRRPXITB-QGZVFWFLSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-(5-methoxy-3-methylpyrazol-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=C(C=C1OC)C KHJVGVHRRPXITB-QGZVFWFLSA-N 0.000 claims 2
• BLMHXOHJXHHGKN-HXUWFJFHSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-[4-(1-methylpyrazol-4-yl)pyrazol-1-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C=1C=NN(C=1)C BLMHXOHJXHHGKN-HXUWFJFHSA-N 0.000 claims 2
• PWEYRABKJOCWSK-HXUWFJFHSA-N 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]-3-[4-(2,3-dihydrofuran-4-yl)pyrazol-1-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC1=C(C=C(C=C1)F)[C@@H]1N(CCC1)C1=NC=2N(C=C1)N=CC=2N1N=CC(=C1)C1=COCC1 PWEYRABKJOCWSK-HXUWFJFHSA-N 0.000 claims 2
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